4-Hydroxy-6-alkyl-2-pyrones as nucleophilic coupling partners in Mitsunobu reactions and oxa-Michael additions

Michael J. Burns, Thomas O. Ronson, Richard J. K. Taylor and Ian J. S. Fairlamb
Beilstein J. Org. Chem. 2014, 10, 1159–1165. https://doi.org/10.3762/bjoc.10.116

Supporting Information

Supporting Information File 1: Detailed experimental procedures, characterisation data for compounds 3b–e, 4a–l, 5d, 7a–i and 9 and 1H NMR spectra for novel compounds.
Format: PDF Size: 2.3 MB Download

Cite the Following Article

4-Hydroxy-6-alkyl-2-pyrones as nucleophilic coupling partners in Mitsunobu reactions and oxa-Michael additions
Michael J. Burns, Thomas O. Ronson, Richard J. K. Taylor and Ian J. S. Fairlamb
Beilstein J. Org. Chem. 2014, 10, 1159–1165. https://doi.org/10.3762/bjoc.10.116

How to Cite

Burns, M. J.; Ronson, T. O.; Taylor, R. J. K.; Fairlamb, I. J. S. Beilstein J. Org. Chem. 2014, 10, 1159–1165. doi:10.3762/bjoc.10.116

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Ewan, H. S.; Biyani, S. A.; DiDomenico, J.; Logsdon, D. L.; Sobreira, T. J. P.; Avramova, L.; Cooks, R. G.; Thompson, D. H. Aldol Reactions of Biorenewable Triacetic Acid Lactone Precursor Evaluated Using Desorption Electrospray Ionization Mass Spectrometry High-Throughput Experimentation and Validated by Continuous Flow Synthesis. ACS combinatorial science 2020, 22, 796–803. doi:10.1021/acscombsci.0c00119
  • Masuda, M.; Sakurai, N.; Ogura, Y.; Murase, T.; Kawasaki, T.; Aiba, S.; Mori, N.; Watanabe, H.; Takikawa, H. Studies toward the enantioselective synthesis of neurymenolide A: Construction of the macrocyclic core via Claisen rearrangement. Tetrahedron Letters 2020, 61, 151825. doi:10.1016/j.tetlet.2020.151825
  • Obi, G.; Chukwujekwu, J.; van Heerden, F. R. Synthesis and antimicrobial activity of new prenylated 2-pyrone derivatives. Synthetic Communications 2020, 50, 726–734. doi:10.1080/00397911.2020.1718710
  • Obydennov, D. L.; El-Tantawy, A. I.; Sosnovskikh, V. Y. Triacetic acid lactone as a bioprivileged molecule in organic synthesis. Mendeleev Communications 2019, 29, 1–10. doi:10.1016/j.mencom.2019.01.001
  • Samanta, S.; Mondal, S.; Hajra, A. A convergent synthesis of vinyloxyimidazopyridine via Cu(I)-catalyzed three-component coupling. Organic & biomolecular chemistry 2018, 16, 1088–1092. doi:10.1039/c7ob02883k
  • Markham, K. A.; Palmer, C. M.; Chwatko, M.; Wagner, J. M.; Murray, C.; Vazquez, S.; Swaminathan, A.; Chakravarty, I.; Lynd, N. A.; Alper, H. S. Rewiring Yarrowia lipolytica toward triacetic acid lactone for materials generation. Proceedings of the National Academy of Sciences of the United States of America 2018, 115, 2096–2101. doi:10.1073/pnas.1721203115
  • Fürstner, A. Gold‐Katalyse für die Heterocyclenchemie: eine repräsentative Fallstudie zu Naturstoffen der Pyron‐Reihe. Angewandte Chemie 2017, 130, 4289–4308. doi:10.1002/ange.201707260
  • Fürstner, A. Gold Catalysis for Heterocyclic Chemistry: A Representative Case Study on Pyrone Natural Products. Angewandte Chemie (International ed. in English) 2017, 57, 4215–4233. doi:10.1002/anie.201707260
  • Bassou, O.; Chicha, H.; Bouissane, L.; Rakib, E. M.; Saadi, M.; Ammari, L. E. Ethyl (E)-2-(2,7-dimethyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-4-yl­idene)acetate. IUCrData 2017, 2. doi:10.1107/s2414314617002085
  • Álvarez-Calero, J. M.; Jorge, Z. D.; Massanet, G. M. TiCl4/Et3N-Mediated Condensation of Acetate and Formate Esters: Direct Access to β-Alkoxy- and β-Aryloxyacrylates. Organic letters 2016, 18, 6344–6347. doi:10.1021/acs.orglett.6b03233
  • Zhou, W.; Zhuang, Y.; Bai, Y.; Bi, H.; Liu, T.; Ma, Y. Biosynthesis of phlorisovalerophenone and 4-hydroxy-6-isobutyl-2-pyrone in Escherichia coli from glucose. Microbial cell factories 2016, 15, 149. doi:10.1186/s12934-016-0549-9
  • Shin, U. S.; Joo, S.-R.; Kim, S.-H. Zinc Enolate/Sulfinate Prepared from a Single-Run Reaction Using Zinc Dust with O-Tosylated 4-Hydroxy Coumarin and Pyrone. Bulletin of the Korean Chemical Society 2016, 37, 1144–1147. doi:10.1002/bkcs.10819
  • Ronson, T. O.; Burns, M. J.; Voelkel, M. H. H.; Evans, K. J.; Lynam, J. M.; Taylor, R. J. K.; Fairlamb, I. J. S. Total Synthesis and Stereochemical Revision of Phacelocarpus 2-Pyrone A. Chemistry (Weinheim an der Bergstrasse, Germany) 2015, 21, 18905–18909. doi:10.1002/chem.201504089
  • Ronson, T. O.; Voelkel, M. H. H.; Taylor, R. J. K.; Fairlamb, I. J. S. Macrocyclic polyenynes: a stereoselective route to vinyl-ether-containing skipped diene systems. Chemical communications (Cambridge, England) 2015, 51, 8034–8036. doi:10.1039/c5cc02091c
  • Yao, H.; Song, L.; Liu, Y.; Tong, R. Cascade Michael addition/cycloketalization of cyclic 1,3-dicarbonyl compounds: important role of the tethered alcohol of α,β-unsaturated carbonyl compounds on reaction rate and regioselectivity. The Journal of organic chemistry 2014, 79, 8774–8785. doi:10.1021/jo501604e
Other Beilstein-Institut Open Science Activities